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Five By Twenty-Five: Retrospective Advice to My Twenty-Year Junior

Recently, I have received invitations to work related training events, all on the topic of “getting to the next level,” or in my world, making the jump from middle management to executive leadership. This is in addition to webinars, segments of other training events and countless articles on the topic. The issues being addressed are assessing the need for succession planning and how to prepare the next round of leadership to move into senior positions (having failed at the task for the last ten years or so). Feeling so close but so far from such a promotion, this got me to thinking about my mindset from twenty years ago, in contrast to some valuable lessons I have picked up along the way. Being inspired by Jeff Haden’s, What Would You Tell the 25 Year-Old You?, I came up with my own, “Five by Twenty-Five” list of things I would advise myself…twenty years ago.

What to Read

First, there are a number of books I would recommend. I would stick to titles of a more timeless nature that offer guiding principles in any age of technology or innovation, rather than something tied to a current trend. I would also recommend a number of historical titles to show that many challenges we face are not entirely new, and that there are solutions available just like there have been in the past.

What to Interpret from a Successful Person

I would explain that when you look at a successful person, i.e.: someone who has accomplished much in their life and career or who is where you think you might like to be in your career, remember that you are looking at a current snapshot of that person, and not the work, struggle and learning experiences getting there. So be patient!

What to Plan

I would explain the need to formulate a strategic plan for my own career, and how to plan the deliverables that it would take to get there. Within the scope of this plan, I would explain the need to be fairly specialized early on, at least in terms of industry expertise. Many who have succeeded (though not all to be sure) have done so within the scope of a particular industry. So choose an industry that is interesting to you, has a demonstrative future and one that you might have purpose and fulfillment participating in.

What to Contribute

I would explain the principles of creating value within an organization, and that you will succeed most by helping move the organization forward, while helping achieve its mission and vision. I would pit this in stark contrast to the idea that an organization exists to provide someone their current job.

What to Imagine and Demand as a Leader

Related to the last item, I would explain the need to be visionary as a leader, and how to lead others in expanding their ideas and approaches to problem solving. I would explain that nearly all sociological aspects of management eventually lead to change management, and that this is one of the most felt challenges in leadership.

I would explain the need within the scope of leadership to create an environment of personal accountability, clear expectations for myself and staff, and how the team is always able to do more together when personal excellence in their work is joined with real and essential collaboration.

There are many others of course, beyond this list, but these are five broad swaths of leadership, strategy and philosophy of work, each of which can be filled in with many applications driven by particular circumstances, giftedness and temperament.